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Now and Then, Here and There. Inspired by children soldiers in Africa. The overall story is one of hope, but much of the content can make you forget that theme. Do not be fooled by the first episode.

Gungrave is largely a reflection on the past that lead to the present predicament the characters find themselves in. Like most reflections on the past, the story follows these character's lives from young adults with their happy future ahead of them, to the rather depressing present that they all find themselves in now.

Tokyo Magnitude 8.0, if you connect with the characters, should bring you close to metaphorical tears by the end. If you don't connect with them, then it won't. Covers a few days after a large earthquake hits Tokyo.

Grave of the Fireflies is sort of the go-to anime for the "tears" category. It brings into focus the travails and tribulations of a young boy and his younger sister trying to survive in the immediate aftermath of WW II. For the record, it makes Tokyo Magnitude 8.0 seem like an episode of Family Guy, so if you find any tears in Tokyo Magnitude 8.0, Grave of the Fireflies may be too much for you.

Mobile Suit Gundam, Zeta Gundam, Char's Counterattack. The glorious triple threat of the golden age of the Gundam franchise also happens to have been written during Tomino's darker days (Urobuchi Gen really has nothing on Gen when it comes to depression). If that's just too much Gundam to absorb, Victory Gundam serves as a decent stand alone substitute, also written during Tomino's darker days.

Depending on one's perspective, the Nana manga is full of tear-worthy moments, including where it left off when the writer stopped writing (I actually think where it stopped was almost uplifting in a way, but I think I'm in a very small minority).

And, this list could go on, and on, and on, and on, so I'll end with Berserk. Either the tv series, or the recent movies. To this day, still one of the best fantasy animes ever made, with none of that cloying lightness and rainbows stuff.

For a manga try March Comes in Like a Lion, I find it very touching and it certainly has it's sad moments, although it has uplifting ones too. From the same mangaka as Honey and Clover if that means anything to you (which you should also watch if you haven't already).

Can't See Can't Hear But Love certainly got me choked up at times, although the characters can be somewhat frustrating, definitely worth reading though.

I'm trying to encourage anyone I can to read All Rounder Megeru it's not touching nor does it have a crazy plot twist but it certainly not your average series. It's the most realistic martial arts manga/anime I've ever seen and is one of the most addicting series I've read in some time. I normally shy away from anything involving martial arts but I couldn't put this down.

If you haven't watched/read Usagi Drop then you've really missed out. One of the most touching series I've ever watched. Following the manga there is a time jump and the ending is somewhat controversial involving a fairly major twist.

In a similar theme to Usagi Drop is My Girl a very touching story about a man who finds out that his ex-girlfriend has died leaving him with a 5 year old daughter he didn't know existed. No plot twists though.

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If you can't dazzle them with brilliance baffle them with bullshit ~Coach Davids

More of a manga reader now than an anime watcher. Currently reading list here

I'm going to recommend a favorite of mine, Full Moon wo Sagashite.
A lot of the anime is funny and easy to watch. It may even seem like filler. Rest assured, once you get to the second season, the plot takes off and there is a definite twist. I've cried more watching this show than anything else I can remember, even the second, third, fourth and fifth time through.
On the other hand it may be too much "romance" for you to consider a palate cleanser. Well, a lot of these other suggestions are romance too.

I can also second Saikano, it's incredible. Actually I like all of Azuma Denton's suggestions except 5cm Per Second and Air. I didn't like either one at all.

I'll also recommend Chrono Crusade. It's action based and takes place on earth, focusing on demonic warfare. It culminates into the most tragic ending I've ever seen. I was ranting for two weeks about the ending to anyone who would listen to me.

Not meaning to criticize anybody's tastes, but why do people like tragic endings in fiction? I mean, there already are so many of them in real life (consider the documentaries about children dying in Africa for example). What's the point of turning fiction tragic as well?
Just asking.

Realism. While happy endings are good and make you feel better they also tend to have negative effect, at least on me.

Happy endings make you dream about things that have barely any chances of becoming real. When you realize that your dreams can come true only in fictional world, it is far more depressing than watching drama.

Drama gives a more realistic take on life so your hopes are not high. Besides drama tends to go over board sometimes and then you realize that you life is not as shit as you thought.

It is a reverse psychology for me.

Not that I don't watch and enjoy comedies. But drama never hurts from time to time.
And it makes things more engaging and surprising. I always go "Yeh, he will survive. Yeh, they'll be together as always." and then BAM! "Oh, that's a surprise!"

Not that I don't watch and enjoy comedies. But drama never hurts from time to time.

I agree. However, sometimes things get extreme. For example, during my whole time at school and university I can't remember even 2 books with happy endings among those they made us read. It's as if a work of fiction with a happy ending was automatically excluded from the concept of "work of art" just because it's not sad.

Sorry as what I am saying is kind of off-topic here as the thread is about recommendations of tragedies.